The Best Underwear for Any Situation

The right pair of underwear can make the difference between a good flight and a bad flight, or can give you the extra confidence to ask for that promotion you’ve been working towards, or to approach the woman of your dreams. We turned to Michael Kleinmann, Editor-in-Chief of The Underwear Expert, to help pinpoint the best underwear for different situations. (You can thank him when you get that raise, catch that flight, or win that game.)

Moisture management in this brief and waistband means a dry wear from the top down during even the most heated board meeting. The 90 percent nylon/10 percent spandex fabric means an ultra soft fit, and the contour pouch means lift and support for the boys all day long. Designed to prevent the legs from rolling up and sculpt to the body for maximum comfort, these briefs are a sure bet. $28

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The Suit & Tie Office

2(x)ist Pima Cotton Contour Pouch Brief

Made with an unbelievably soft cotton, this mid-rise brief falls right on your hips. The contour pouch will keep you lifted through even the longest workday. Tagless for extra comfort, this brief is one of the most comfortable you’ll find. $20

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The Suit & Tie Office

Calvin Klein Knit Boxer Brief

This soft, 100 percent cotton brief is the button-fly version of the classic Calvin Klein pair that Marky Mark made famous in the 90s. The classic and comfortable brief sports a 2 button front fly and a Microfiber waistband. It’s a classic brief for a reason: well made, comfortable, and perfect to wear everyday. $33

With an elasticized waistband and ultra-lined front, these briefs provide maximum comfort. The soft cotton and elastane blend fabric will keep your game sharp. The minimalist design is appropriate for day or night, no matter your goal. $15

You’ve nailed the perfect job. You can climb the corporate ladder and still have fun. Support and comfort are as important as feeling energetic and irreverent from the inside out.

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The Laid Back Office

Pull-in Fashion Fraises 12 Strawberry Boxer Brief

This pull-in boxer brief has been a best seller for the brand for over 10 years, and for good reason: The 85 percent polyester/15 percent Lycra is super soft and cool on the skin. They breathe well and keep you supported, but not constricted. $40

Sueded microfiber fabric makes this Calvin Klein favorite one of the softest pairs out there. Bright spring colors with names like like Banana, Parasail and Solar Blue, will keep your mood light, no matter what the season. The low-rise designs are ideal for low-rise jeans and the tagless detail means seamless comfort all day long. Plus, its contour pouch means you’ll get a little more attention up front, too. $28

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The Laid Back Office

2(x)ist Military No Show Trunk

This pair of underwear has it all. It’s sleek, masculine, and most of all—comfortable. The fabric is a modal, cotton and spandex blend with a texturized and sturdy feel. It’s professional, remarkably supportive, and breathes well—without sacrificing personality. $28

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The Gym

If you’re meeting the boys at the gym after work, or going for a quick jog on the weekend, you’ll need a pair that maintains its shape while also keeping you cool and dry.

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The Gym

Under Armour M Series Boxerjock Brief

For an active lifestyle, you need an actively awesome pair of underwear and this lightweight, anti-microbial, and comfortable boxer brief is just about as good as you can get. Made with a slick and smooth mesh fabric, it gives ultimate comfort, breathability and a range of motion (thanks to its four-way stretch fabrication). The built-in Moisture Transport System means it wicks sweat away to keep you cool and dry. $20

Science, meet underwear. This trunk provides a moisture-wicking waistband and parallel side panels to create a moisture barrier between the package and the inner thigh. An articulated, seamless front pouch allows your area to rest naturally. Non-restrictive support means you can keep your mind on the game when it matters most. $29

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The Gym

Tommy John 360 Sport Trunk

This trunk is the underwear equivalent of a Swiss Army Knife. Offering a horizontal fly for "quick" access, a contour pouch that supports, comforts, and lifts, 360 degree stretch fabric, zoned ventilation to keep you cool and dry during even the most intense activities, anti-odor technology that prevents the growth of odor causing molecules and perhaps most importantly, a utility pocket, for everything from iPods to cash, this underwear has it all. With a clean and sharp design, this underwear was made to both feel and look incredibly great. $29

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Date Night

Underwear is a key ingredient to a successful date; knowing you can confidently shed your pants without hesitation is a powerful thing.

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Date Night

Rated M Elementary Boxer Brief

Mario Lopez’s new line is made with a polyester, spandex and cotton blend. The boxer brief perfectly sculpts to the body with a sleek texture and intensely smooth fit. Falling below the natural waistline, it has a contour pouch that accentuates and supports. The back printed logo on these sleek briefs will make you feel like a star. $20

With a 40 percent modal viscose and 60 percent cotton blend fabric, this trunk from C-IN2 is perfect for the man who appreciates the finer things in life. It breathes well, supports and has a low-rise so you can wear it with dress pants or jeans. Muted colors add a little excitement to any suit, though with a heat transfer tag, you’ll forget your wearing these at all. $30

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Date Night

Calvin Klein Bold Brief

Lightweight and breathable, these classic briefs offer a body-defining fit and just enough stretch. A stealth logo on the back makes these briefs stand out from both sides, and the cotton and Lycra blend fabric provide a 360 degree deluxe contoured view for anyone that sees you in them. Bonus: It comes in awesome color options. $24

Whether you’re watching a game with friends or doing work around the house, you’ll probably want to wear something comfortable that allows you to hang loose.

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Lazy Weekend

C-IN2 Hand Me Down Runner Boxer

This vintage collegiate cross between an 80s runner short and traditional boxer is one of the most comfortable loungewear items available. With a faded fabric, you’ll want one in every color. $26

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Lazy Weekend

Calvin Klein One Slim Fit Boxer

These sleek and slim fit shorts are more fitted than traditional boxers without being constricting. Made with a stretch microfiber fabric, this boxer is a perfect pair for the guy who likes to relax but still look good at home. The cool, soft feel against the skin means you’ll be able to cozy up without overheating. $24

This brief is literally made to relax in front of the television. With a built-in pocket over the pouch, you can keep your remote or phone close. For the guy who likes to keep a hand down there, the pocket gives you an excuse. With a seamless tag, pima cotton elastane blend fabric and low rise design, you’ll be giving this pair a high five all weekend. $25

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In Flight

Traveling is hard enough. Add a lackluster pair of underwear that doesn’t breathe and agitates your skin and a 5-hour flight will feel like a helicopter ride to Hong Kong.

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In Flight

Jake Joseph Brief

Wonderfully soft to the touch, this pair is the epitome of breathable, with its silk-like fabric. Constructed to provide equal amounts support and comfort, this brief will give you plenty of reasons to travel. Plus, the bamboo viscose fabric is naturally anti-microbial, which means you can stay clean and smell good on even the longest trips. $37

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In Flight

2(x)ist Touch Trunk

Made with a moisture wicking microfiber fabric, this ultra-contoured trunk will keep you dry and at ease. The trunk cut means you get support and coverage without bulky fabric under your clothes. $28

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In Flight

Sly Boxer Brief with Pocket

Prefer to keep it classic when you travel? Try these boxer briefs that fit like a glove. Made with a 95 percent cotton and elastane fabric and enhanced by a nylon and elastane waistband, this brief will live up to even the highest standards. This design is a favorite, and perfect for the guy who likes a little color under his pants. The coolest detail on this boxer brief: The pocket on the right leg for, well, wherever your travels take you. $25

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